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Don’t beat yourself up over spending… try this instead.

Don’t beat yourself up over spending… try this instead.

November 16, 2023

I've spent countless hours of my life talking with people all over the world about money.

During these conversations, one theme comes up again and again.


Almost everybody has an idea of what the financial life of their dreams would look like.

Almost nobody has a plan for how to get there.

After having hundreds of conversations about this subject, We've come up with a strategy that may help.

But first, a couple of disclaimers:

1- It’s hard. Kind of like when your doctor tells you to eat more vegetables and exercise for at least an hour a day.

2- It’s boring. Like watching an oak tree grow. Think short-term boring but long-term exciting.

For those of you I didn’t lose at hard and boring…

Step 1: Pay attention to your spending.
Call it budgeting if you want, but I'm essentially talking about paying close attention as you spend money. This could be as simple as keeping an index card in your pocket and writing down every transaction or purposefully reviewing your monthly credit card statement. Whatever your method, just start noticing how you’re spending money.

Step 2: Find wasted money.
The hard part of saving isn't saving itself. The hard part is finding the money to save. Not long ago, I figured out a routine that helped. I printed out my credit card statements and went through each charge. On one statement, a few lines down on the second page, I found a charge for GoGo internet service. That’s the internet service available while flying on many airlines. I recall the charge being $39 per month for unlimited access. After highlighting the charge, I leaned back in my chair, deep in thought. How long had it been since I last got online at 35,000 feet? In a moment of Zen-like clarity, I realized I hadn’t even been on a flight that month. I did the math and discovered it had been more than a year, 13 months to be exact, since I had used this service. For 13 months, I'd been paying for something I wasn’t using. I'd wasted more than $500. It's crazy I let it go on for that long, but I'm glad I found it!

Step 3: Automate savings.
If anything qualifies as exciting, perhaps it's this: I just found $39 per month to start saving. Because I was already spending that money, it wasn’t even going to hurt. All I had to do was log in (not at 35,000 feet) and set up an automatic investment for $39. Don’t get hung up on finding the best investment. That reeks of excitement, and we’re not into that. Just do something boring, like a Vanguard S&P 500 fund, or send the $39 to your kids' 529 accounts. The important part is automating the behavior. Just have the money pulled regularly from your checking account and put into whatever boring saving or investment vehicle you decide. No stamps, envelopes, or willpower required.

Step 4: Repeat.
At the risk of making the plan sound fun, what if you decide to turn it into a game? Kind of like a treasure hunt! Every month, pull out your credit card statements and carefully take notice of every charge, look for wasted money, and add it to your automated savings. See how often you can move that number up. See if you can start a streak and raise the amount each month, even if it's just $5 or $10. I know it may sound boring to save $39, then $50, followed by $65, or even $67 (those two bucks matter). But over time, those dollars add up. How high can the number go?

We recommended to one of our clients to try this. They paid attention to their spending, found wasted money, automated their savings, and repeated their actions for longer than a decade.

When they started, they had a goal of having $1 million dollars. 

Then, one day, we were able to give them a call. "You did it! You just crossed the $1 million mark."

Yes, it took a long time of consistently doing boring things, but they reached their goal.

And all it took was doing four boring steps repeatedly.

Hope that helps.